Synthesis and photoluminescence study of di‐dendron dendrimers derived from mono‐Boc‐protected ethylenediamine cores

Abstract

This work is focused on the synthesis and optical properties of cone-shaped structural feature di-dendron polyamidoamine dendrimers up to the third generation with mono-Boc-protected ethylenediamine (EDA) as a core. Strong UV absorbance spectra and fluorescence spectra from di-dendron dendrimers with different terminal groups (-NH(2), -COOCH(3)) were studied under different conditions by varying experimental parameters such as concentration and pH. The optical density and fluorescence intensities increased when di-dendron dendrimers generation number increased from 0.5 to 3.0. It was confirmed that the concentration of di-dendron dendrimers plays an important role in fluorescence intensity. The increase in fluorescence intensity was linear in low concentration regions, but the intensity increased slowly in high concentration regions. The results also showed a rapid increase in fluorescence intensity at low pH. The formation of a fluorescence-emitting moiety had a close relationship to protonated tertiary amine groups in di-dendron dendrimers derived from mono-Boc-protected EDA cores. Furthermore, the formation of fluorescent chemical species was irreversible.

Amphiphilic water soluble cationic ring opening metathesis copolymer as an antibacterial agent

“…In the first part of the synthesis, pure exo isomer of oxanorbornene derivative (1) was synthesized by the combination of furan and maleic anhydride in THF through Diels‐Alder cycloaddition . (see the NMR spectra at Figure S1 and S2) The NH 2 group of EDA was protected with BOC followed by reaction of the EDA‐BOC with oxanorbornene for the formation of compound 2 . (see the NMR spectra Figure S3 and S4) Deprotection of compound 2 was carried out by the addition of TFA for the formation of the amine containing compound 3 .…”

Crystallization‐Induced Emission Enhancement of a Deep‐Blue Luminescence Material with Tunable Mechano‐ and Thermochromism

“…We synthesized the compound P1 (Scheme S1, Supporting Information) with 1,8‐naphthalimide derivative as the peripheral fluorophore and poly(amidoamine) as the linker (Scheme S1, Supporting Information). Compound 1 was synthesized by using di‐ tert ‐butyl dicarbonate (a Boc reagent) that reacted with ethanediamine, then the Michael addition reaction of compound 1 and methyl acrylate (MA) gave compound 2, and poly(amidoamine) (compound 3) was prepared by the reaction of compound 2 with ethanediamine in methanol at room temperature . Finally, the target molecule P1 was obtained as a white powder via a simple one‐step reaction, as depicted in Scheme S1 in the Supporting Information.…”

Near-Infrared Emitting Poly(amidoamine) Dendrimers with an Anthraquinone Core toward Versatile Non-Invasive Biological Imaging

“…More recently, the same hydrophobic fluorophore was conjugated with hydrophilic poly­(amidoamine) dendrons to obtain a series of fluorescent dendrimers with enhanced water solubility for fluorescence imaging under biological conditions . Another example has been reported by Christensen et al with the synthesis of a dendrimer with a single sulforhodamine B molecule as the core. , Several works were also devoted to the development of fluorescent macromolecules with poly­(amidoamine) dendrons functionalized with chromophores localized at the focal point and/or at the periphery of the dendron. − It is important to note here that none of these works were targeted at the development of NIR absorbing and emitting poly­(amidoamine) dendrimers.…”